Dimethylamine → 7-amino-4-[4-(dimethylamino)cyclohexyl]-2-methyl-2,3-dihydro-1H-isoindol-1-one

Participants

Reaction Steps

A solution of 7-amino-2-methyl-4-(4-oxocyclohexyl)-2,3-dihydro-1H-isoindol-1-one (100.0 mg, 0.3871 mmol) in 1,2-Dichloroethane (2.0 mL) was charged with 2.0 M of dimethylamine in THF (0.2903 mL, 0.5807 mmol) and sodium triacetoxyborohydride (164.1 mg, 0.7743 mmol). The reaction mixture was stirred at rt for 24 hours. The reaction mixture was quenched with NaHCO3 (10 mL) and extracted with EtOAc (20 mL). The organic layer was washed with brine (10 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to yield a light yellow oil. The crude material was purified by silica gel chromatography on the combi-flash Rf system using DCM/7M NH3 in MeOH (100:0→90:10) as eluent. The fractions containing product were combined and concentrated under reduced pressure to yield a light yellow solid, 64.7 mg (58% yield). 1H NMR (CDCl3, 400 MHz): δ=1.53 (d, J=11.12 Hz, 4H), 1.91 (d, J=11.12 Hz, 2H), 2.08 (d, J=14.65 Hz, 2H), 2.31 (br. s., 6H), 2.45 (br. s., 1H), 2.48-2.58 (m, 1H), 3.14 (s, 3H), 4.30 (s, 2H), 5.07 (br. s., 2H), 6.57 (d, J=8.34 Hz, 1H), 7.26 (br. s., 1H). MS (ES+): m/z 288.21 [MH+] (TOF, polar).

Provenance & Evidence